


experiences & experiments

by Rinniebee



Category: Gilmore Girls
Genre: F/F, F/M, Graphic Description, Lets just say they get down and dirty okkkk, OT3, Oral Sex, Sexual Content, Threesome
Language: English
Status: Completed
Published: 2017-01-18
Updated: 2017-01-18
Packaged: 2018-09-18 07:47:21
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,213
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9375074
Author URL: https://archiveofourown.org/users/Rinniebee/pseuds/Rinniebee
Summary: "Well," she bit her lip, "what was the previous arrangement exactly?""When you want to see me, you tell me. I make time to come down. When I'm here we're together and when I'm not, we're not."Jess/Avery/Rory smut.





	

**Author's Note:**

  * For [theedgeofthedesert](https://archiveofourown.org/users/theedgeofthedesert/gifts).



> Hey all!
> 
> So this isn't TECHNICALLY apart of be that as it may/iron hearts all turn to rust, but it can be if you want it to be. At the end of the day I just wrote some OT3 smut because the actual Iron Hearts All Turn To Rust probaaaably won't go this route. So if you wanted Rory and Avery to hook up, all your dreams have come true here! And if you didn't then turn back!! Turn back now!! 
> 
> Anyway, as always don't forget to leave a comment!! Also blame Edge/Sam for this. OK BYEEEE

Tonight was a good night in Jess' opinion.

It was just him, Rory, and Avery. At first he thought the three of them going out would be weird. It was intended to be Rory and Avery's girls night after all, but Rory had forced him to join in.

She and Avery been getting to know each other more, hanging out without him whenever Avery could get away from Boston. He didn't mind, really. In the end, Jess thought it was a good thing that the two of them were getting closer. There was no need for him to play middle man anymore, and all the jealousy between them had dissipated by now. Jess thought it had a lot to do with Rory's little crush, and he teased her about it, liking the way her face got beet red whenever he brought it up. Eventually she'd gotten tired of it, promising that one day she'd get him back, but he hadn't taken her seriously until tonight.

The bar wasn't too busy, so it wasn't horribly loud, which Jess greatly preferred. He liked being able to actually hear the conversation at his table without having to yell or get super close to the other persons ear. They talked amicably, had some drinks, and ordered some food before paying the bill and heading back.

Avery asked if they could walk her to her hotel, and Jess and Rory didn't really mind. It was summer 2009 and the Philadelphia streets were humid in that stifling way that Jess really hated. Avery's hotel wasn't far, but she invited them up when they stepped into the lobby. Jess and Rory walked clasped hand in hand behind Avery, only splitting off when Rory went to explore the suite.

It was a beautiful hotel. Spacious and clean with a large bed that seemed too big for Avery's petite frame. Jess took a quick look around before suggesting he and Rory take their leave.

"We should let her sleep," he said.

Rory pouted at him from the bathroom doorway, made her way over to Avery and hugged her. "But if we leave now then when we wake up she'll be on her way to the airport."

"Rory, you can't hog her all night," Jess chided.

"Yes I can," his girlfriend mumbled. "She doesn't mind. Do you, Avery?"

Avery smiled at her. "I'm flattered."

"See," Rory said smugly. "She's flattered."

Jess rolled his eyes and took a seat on the bed. "Fine, we'll stay for a bit." He didn't expect her to last long. Drunk Rory was either one of three things: horny, tired, or hungry. He'd get her out of here soon enough.

"Yay!" Rory let go of Avery and made her way over to the bed to sit beside him. She leaned into his side and kissed his neck. "Thank you for indulging me."

"Mmmmhm," he hummed with a small smile. They both watched Avery pull out something to wear for bed before she slid off to the bathroom, promising them she'd be right back.

Rory scooted back on the bed with a childlike grin before falling back into the pillows with her arms spread open wide. "Ahhh," she sighed happily.

"Enjoying yourself there, Gilmore?" Jess teased.

"Come join me," she said, biting her lip with darkened eyes. Jess felt a jolt in his groin but he kept himself grounded, glancing back at the bathroom door.

"When we're at home we can do anything you want," he promised, knowing Avery didn't deserve this. Jess loved the thrill of getting caught as much as Rory, but there was a big difference between getting caught, teasing their friends, and being straight up disrespectful to his ex.

Rory stared at him with an odd look he couldn't place. It almost made him feel nostalgic, though he couldn't quite figure out why. She took her eyes off of him just as Avery came out from the bathroom dressed in a pair of black silk shorts, a matching tank up, and her curly hair up in a big bun that reminded him of their high school days. Rory's eyes flickered over his ex girlfriends form and she licked her lips, cheeks wonderfully red. Maybe this crush went a bit deeper than he'd originally been led to believe.

Avery smiled at the two of them and crawled into bed next to Rory but she stayed over top of the covers. "It's comfy, right?"

Jess glanced from his girlfriend to his ex, curious about this budding relationship. He noticed the way Rory slid a little closer to Avery, her already short dress inching up higher on her thighs. Avery seemed to follow her lead, shifting her right leg forward a little bit until her shorts started to ride her and he could see the edge of a single ass cheek.

He wanted to ask if they'd done this before, but they both seemed a little too shy for that to be the case and Jess didn't believe that Rory would cheat on him, anyway. Even if she'd gotten the idea, Avery would've never let it fly. He looked away from them for a moment, unsure of what to do, but when he looked back Rory was staring at him.

"Can I... kiss her?" Rory asked him a little tentatively, confirming that she had, in fact, never done this before. That made him feel a little better. "You're my boyfriend and I don't want to make you angry but..."

Jess shook his head, not really minding where this was going. "Go ahead," he said, voice hoarse. He could feel the pressure of his jeans building against him already.

Rory turned back to Avery, who hadn't stopped staring at her at all. "Can I kiss you?" Rory asked her next, and Avery only answered with a smile.

His ex wrapped her leg around Rory's completely, dragging her in closer before their lips met. It was a soft kiss, Jess thought. Not overly passionate or sloppy. Just soft and sweet. Rory cupped Avery's cheek with her hand and pressed herself into her just before pulling away.

"How was it?" Avery asked, eyes twinkling.

"Good," Rory whispered, and Jess knew by her tone of voice that it was more than good. Definitely a better experience than Paris Geller.

His girlfriend pushed herself up to grab his hand and tugged him closer to them. When he was finally within reach she kissed him, too, almost as if she were comparing. Jess groaned into her mouth as the kiss quickly turned hot and dirty. Rory found purchase in his hair, and he reached for her but it was over before he could grasp her waist. Her eyes were fully blown, just a tiny rim of blue left, when she looked at him just before she looked at Avery and then back to Jess with her eyebrows raised, and Jess finally understood what she wanted. Luckily, so did Avery.

His ex sat up and scooted herself closer to him before getting up on her knees, her hand snaking up his chest before she clasped the back of his neck and captured her lips in his. It'd been a year since he'd kissed her last, but it was exactly like he remembered. She kissed him longer than Rory had so he grabbed her hip and put his other hand on her ass to squeeze it just before the kiss ended.

"So," Avery asked, looking between them, "what's the plan?"

"This is Rory's fantasy, I think," Jess said, looking at his blushing girlfriend. "We do whatever she wants."

"Okay," Avery agreed. "What do you want, Rory?"

"I want both of you," Rory whined, her words a little older than anything he'd expected from her. "I can't choose."

"You don't have to choose," Avery promised her, moving in a little closer. She placed a kiss on Rory's cheek, then moved to her jaw before sucking at her neck. Rory breathed out a little quiet moan, leaning her head back to give Avery more access.

Jess moved in, straightening out Rory's legs as Avery got her to lay down flat on her back. He shoved her dress up to her hips and spread her legs, massaging gentle circles into her inner thighs. He kissed from her knee cap up to her panties and then pulled them down in one quick motion, throwing them away to the corner of the hotel room. As fast as her panties were gone, his mouth was on her and she was keening. They hadn't done much to her but she was already dripping onto the bed sheets. Jess slipped two fingers into her with ease, curling to stroke her g-spot as he sucked and lapped at her clit just the way she liked it.

He looked up to see Avery swallowing Rory's moans into a dirty kiss and Jess hardened at the sight of their tongues swirling together and taking turns exploring each other's mouths. Jess closed his eyes, feeling like he was going to lose control any moment now. He focused on getting Rory off, flicking her clit with his tongue before sucking it into his mouth and then laying his tongue flat against it in a solid, hard lick. Her walls were starting to grip his fingers a little tighter and he finished her off by pumping his fingers a little faster and taking her clit into his mouth one last time.

He heard her scream out, nice and loud and her hand clutched at his scalp as she came. Her thighs quivered and she tried to clamp them down around him in her bliss, but he kept her pressed open with one hand and slowly came up for air.

Avery was sitting back on her feet, taking the scene in with dark eyes. Jess kissed Rory, soft and slow before whispering, "Good?" into her ear and his girlfriend nodded, still trying to catch her breath.

He smirked at her before sitting up and nodding Avery over to him. She sat up on her knees and wrapped an arm around his shoulders as they kissed. Jess let her explore his mouth to get a taste of Rory. He broke the kiss to put his still wet fingers into her mouth and she sucked Rory off him greedily, applying the same pressure to his fingers as she would to his cock. It took everything in him not to guide her there and find release in her mouth.

Jess looked down at Rory and pulled his fingers from Avery's mouth. "What next?"

Rory pushed herself up on her elbows. "I... want to pleasure Avery but I don't really know how..." She looked adorable when she was embarrassed during sex--especially right now after an orgasm with her hair all wild and her dress completely disheveled.

"You want me to show you?" Jess asked, not completely shocked when Rory nodded her head yes. He still remembered how she said she liked it when he'd touched Avery at the bar last year. That was the first night he'd ever made Rory orgasm, though he hadn't done much other than provide his thigh for her to grind on.

"Okay," he said, pulling Rory to sit up properly before laying Avery down flat on her back. "Avery's pretty easy to please."

"Hey," Avery joked beneath him and Jess smirked down at her.

"It's a good thing. I promise." He slid his hands up from the top of her hips all the way to her breasts, squeezing them softly. She was bigger than Rory, but not by much, they both were able to be covered completely by his hands. Jess pushed her lingerie to the side to expose her and looked back at Rory with his eyebrows raised. "Avery likes foreplay. A lot of it."

Rory licked her lips and nodded, even in her drunk state Jess could tell she was taking notes.

"She likes to be kissed on her neck." He hovered above her before leaning down to pepper a few kisses there, focusing on the hollow of her throat as he sucked. Avery breathed hard beneath him and he knew he was in the right spot. "She likes it hard, she likes bruises." He licked a path to the side of her neck and then nibbled at her skin before sucking the irritation and grinning to himself as Avery moaned her approval.

"And when it comes to her breasts," he pushed himself up a bit so Rory could see, "you can give her a nipple orgasm if you just focus." Jess pinched Avery's nipples and pulled them forward a bit. "Don't be too rough with them, her breasts are really sensitive... just tweak them nice and soft with a little bit of pressure and roll them between your fingers. She likes when you suck but not too much and not too hard. Just soft little kisses with some suction." He demonstrated what he meant and let go of one of Avery's breasts as he kissed the other, using his free hand to bring Rory a little closer. "You try," he instructed.

Rory seemed a little shy at first, looking to Avery for consent. His ex nodded at her, and Rory leaned down to her breasts and took a nipple into her mouth. Avery moaned at both their ministrations, her fingers threaded through Jess' hair. He gently untangled it and moved back, letting Rory take over as he kissed down the expanse of Avery's smooth, toned stomach. He'd almost forgotten that she works out regularly. He didn't move any further down until Rory was ready to move on. Avery was guiding her gently by tugging on her hair and he could tell from the way her back arched that Rory was close to giving her that rare finish. He felt a swell of pride as Avery gasped and held Rory a little tighter to her for a moment before letting her go with a happy, satiated smile.

His girlfriend looked at him with sparkling eyes. "I did it!"

"Proud of you, baby."

Avery laughed. "Come here, Rory."

Rory obeyed and Jess watched as Avery kissed her in show of gratitude. When they broke apart, he hooked his thumbs into Avery's silk shorts and removed them and her underwear at once. He stared at her neatly trimmed pubic hair and took in her swollen lips and the way she glistened once he spread her legs. Rory was back at his side immediately as he started rubbing his thumb back and forth across her slit to spread her arousal.

"Okay," he said, eyes back on Rory. "Avery only likes a mouth down here, really. You can use your thumb to lubricate her everywhere but after that it's all tongue and teeth, okay?"

Rory nodded and Jess smiled. He leaned down flat so he could kiss Avery's inner thighs, the same way he'd done to Rory earlier. He took a deep breath and then dived right in. Jess dragged his tongue up her slit, swirled her clit with his tongue pressed flat and then plunged into her with a hard, flexed tongue. Avery's legs fell open a little more as he tongue-fucked her as deep as he could.

"God, that feels so good," he heard Avery moan, her feet digging into his sides. "Right there, Jess."

Jess brushed her clit with his nose and hoped that Rory could see what he was doing. He tried to catch her eye but her face was contorted with concentration from what he could see. He continued his ministrations on Avery until her moans got louder and her words more incoherent. Her hips started to jerk as she came and Jess shook his head back and forth so his nose rubbed her clit vigorously and she gave a broken sob as her legs trembled and locked around him in her release. He slowed down his licking and removed his tongue from inside of her to lap up any of her extra juices.

Avery's legs loosened and he kissed her just the same as he kissed Rory after getting her off, soft and slow.

"You're still so good at that," she purred.

He smirked at her before turning back to Rory. "You wanna taste her?"

Rory nodded without hesitation and attacked his lips, her tongue plunging deep into his mouth. He grabbed her ass and brought flush up against him, unable to help the way he rubbed his groin against hers. Rory pulled away, brows furrowed as she looked down at his crotch and then back up at him.

"Oh my god, you poor baby! No ones even touched you yet."

Avery quickly got back up on her knees, her hands working fast to rid him of his shirt as Rory worked on his pants. "We're very selfish lovers," Avery said apologetically with a kiss to the back of his ear. "We'll make it up to you, promise."

The only thing he could do was moan. His pants were at his knees and he moved away from their touch to take them off fully, same the his underwear. His cock sprung free and he stroked it to relieve the pressure. Rory tsked at him and pulled his hands away from himself.

"Lay on the bed," she demanded and he did as he was told. Avery and Rory talked quietly among themselves, gave each other a cute little kiss and then bent down on their elbows near his groin. Rory took him into her hand first, pumping him slowly.

"Rory," he complained, closing his eyes. "Please."

"Okay, I won't tease," she promised and took him into her mouth immediately after.

Jess bucked his hips up at the warmth and pressure, almost in tears when she let go. But then Avery took him, and he grabbed her head to keep her down, moaning loud when she took in all of him. He felt eternally grateful to whatever god he could think of that both of these women knew how to deep throat, but then Avery let go too and Jess screamed in frustrating.

"Please," he begged, voice broken as he was practically on the verge of sobbing. "Please one of you just do something. I can't wait another second. Please."

"Ooh," Rory giggled, "I've never made him beg before."

"Me neither," Avery said, sounded just as pleased with herself.

Jess bucked his hips in desperation. "Is that what you want?" He asked, feeling completely delirious now. "For me to beg? I'll beg. I'll get on my knees and fucking beg. I just need to come, please. This is torture."

"We'll save the grovelling for next time," Avery whispered into his ear, licking and nibbling at his ear lobe just as Rory took his tip into her mouth.

"Oh god, yes," Jess moaned, too caught up in his pleasure that Avery had left his side until he felt another mouth on his scrotum. "Oh my god! Fuck!"

They tag-teamed him like that for a while, both of them switching back and forth between who was sucking his cock and who was on his scrotum. He could barely keep it together and his moans just became long winded crooning of their names.

"I'm gonna come," he warned them, and Avery let go of his cock with a pop! and Rory left his scrotum. He thought they were going to start teasing him again to prolong the orgasm, but then he felt both of them on him at once--Rory on one side and Avery on the other. He lifted his head to get a better look at the action and licked his lips at the sight.

"Oh fuck, yeah," he encouraged, watching them bob up and down his shaft together in tandem, practically kissing every time they made it back up to the tip. "God, that's hot. I'm so close."

They moved faster at his words, and he seized up, cock twitching as he came. Avery squeaked a little at the mess he made and he noticed some of it on her brown skin. She swiped at it with her finger and laughed.

"Always messy," she teased him.

He leaned back into the pillows with a happy groan and a laugh. "Fuck, that was so good."

Jess closed his eyes for what felt like a second and didn't wake up until the early morning.

The first thing he heard was the sound of a zipper somewhere in the room. He shifted and Rory groaned unhappily on his chest.

"Don't move," she demanded. "Comfortable."

Someone giggled and Jess tried to make sense of what was happening. He definitely wasn't in his bedroom at home, and he definitely wasn't at Rory's apartment. He blinked at the bright lights of the room and pushed up a little against Rory's will and took in the sight of Avery fully dressed with her packed suitcase.

"Morning," she said making her way over to bed to kiss him. The kiss brought back memories of last night and he relaxed into her lips.

He smiled at her. "Morning."

Avery bent down low to kiss Rory on the cheek. "Morning to you, too."

Rory moaned at her.

"Not a morning person is she?"

Jess shook his head. "You'll learn soon."

"Want coffee," Rory whined against his skin.

Avery laughed. "She's so cute."

Jess placed a soft kiss on Rory's head. "The cutest."

"I'll go get her some coffee."

"Thank you."

He closed his eyes once he heard Avery leave, but he couldn't fall back asleep. Jess sighed and looked down at the girl in his arms. Her breasts were out of her dress and pressed against his skin, but the rest of her was covered for the most part.

She looked up at him, blue eyes bleary with sleep. "Did we... do what I think we did last night?"

Jess nodded. "Sure did."

"Wow," she breathed, but she didn't look regretful. "Do you think we'll do it again?"

"You want to?" He asked.

"I... didn't get to do what you taught me," she said, fumbling with her words a little and blushing.

He grinned at her. "I can't wait to see you do that."

Rory blushed a deeper shade of red and hid her face in his chest. "Shut up!"

He didn't tease her anymore, knowing this was a big step for her. It's taken a year after her initial admission of finding Avery pretty to get them here and he didn't want to take any steps backward. This was a good thing.

"Do you think that Avery wants to continue...?" She asked him a little timidly.

He didn't get the chance to answer as Avery came back in right at that very moment. Rory pushed herself up and fixed her breasts, covering them with the fabric of her dress. She smiled politely at Avery when she saw the coffee.

"Thank you so much," she said, taking the cup.

Avery smiled at her and leaned in confidently to kiss her. He could tell it caught Rory by surprised as she tensed up for a beat, the same way he had, before she melted into it. Rory pushed herself in a little further to deepen it and hummed happily when Avery slowly pulled out of the kiss.

"Coffee definitely does the trick," Avery said to him with a smile.

He smirked back at her. "Who ever thought we'd wind up here? Save for Rory, in her most nasty of dreams."

"Hey!" Rory cried, face red. "I never actually thought this would happen."

"But you're glad it did?" Avery checked.

Rory blushed again but she nodded , taking a sip of coffee.

"Oh, she's very glad," Jess teased, laughing as Rory glared at him.

"So," Avery said, sounding a little serious, "how does this work anyway? Should we start up our previous arrangement?" She was looking at Jess when she asked.

He shrugged. "That works for me? Rory?"

"Well," she bit her lip, "what was the previous arrangement exactly?"

"When you want to see me, you tell me. I make time to come down. When I'm here we're together and when I'm not, we're not."

Rory nodded. "That makes sense. I think I'm okay with that."

Avery smiled. "Great!" She looked back at her suitcase and then at the time on the clock with a heavy sigh. "I'm glad we talked this out because I literally have to get to the airport in about an hour."

Jess moved to get out of bed. He grabbed his boxers and pants off the floor and pulled them on, looking for his shirt. "We'll drive you."

"What? Oh, no. Jess, that's okay I was just going to call a cab."

He found his shirt just as Rory got out of bed and fixed her dress completely, trying to smooth out the wrinkles with her hands.

"No, it's okay," Rory said. "My apartment is just around the corner and I have a car. We'd love to drop you off."

Avery rubbed her arm. "Only if you're sure."

"We are," Jess said, now fully dressed. He pat down his pockets to make sure he had his wallet and keys and then made his way to the door, holding it up for both women in his life.


End file.
